


Not a Race

by annajustice



Series: They're Good Together [5]
Category: Chicago PD (TV)
Genre: Established Relationship, F/M, Friendship, Friendship/Love, Love
Language: English
Status: Completed
Published: 2020-12-10
Updated: 2020-12-10
Packaged: 2021-03-10 00:07:24
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,461
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27985095
Author URL: https://archiveofourown.org/users/annajustice/pseuds/annajustice
Summary: Jay and Will revisit a conversation they had years ago, and this time it has a happy ending. (I promise Hailey shows up later lol)
Relationships: Jay Halstead & Adam Ruzek, Jay Halstead & Will Halstead, Jay Halstead/Hailey Upton, Kim Burgess & Jay Halstead, jay halstead & kevin atwater
Series: They're Good Together [5]
Series URL: https://archiveofourown.org/series/2138988
Comments: 3
Kudos: 65





	Not a Race

Jay pulled up in front of his and Hailey’s now shared apartment, putting the truck in park. “I’ll see you at Molly’s later?” He asked his girlfriend, confirming their plans. 

“Yes Jay.” Hailey said, rolling her eyes. “I will be there at nine, the exact same time I said I was going to be there five times today.” 

“And who are you supposed to pick up?” Jay questioned, smirking at her.

“Trudy.” Jay gave her a pointed look, “I am supposed to fake an emergency, but bring her to Molly’s instead.” 

Jay smiled at Hailey, finding her annoyance adorable. “I love you.” He said, his demeanor softening a bit. 

Hailey’s grumpy look faded and she leaned across the center console, pecking him on the lips. “I love you too.” Jay reached out and pulled her back to him, kissing her again. Hailey smiled into it before reluctantly pulling away. “You gotta go,” she sighed. “How’d you get roped into to doing this anyway?” She asked as she opened the truck door. 

“Kim.” Jay said, and Hailey nodded. “Five year anniversaries are a big deal apparently.” 

“Apparently.” Hailey laughed, shutting the door. Jay rolled down the window, not quite ready to leave yet. “Platt and Mouch better appreciate it, they’ve stolen so much of my Jay time lately.” 

Jay chuckled, “Babe, we work together...and live together. You see me at least twenty-three hours out of the day.”

Hailey shrugged, “It’s not enough.” She smirked at him before heading towards the front door. “I’ll see you later.” 

“Wear something pretty.” Jay called at her, laughing. After he was sure she was safely inside, he pulled out of the parking spot and out of the parking lot. He made the short drive to his brother's apartment, where Will was waiting for him. He was feeling a little jittery, so he opted for the stairs to hopefully wear him out a little bit. “Hey man.” He said, entering the apartment. (He had a key in case Will ever did something stupid...like lose his.)

“Hey.” Will said, getting up off the couch and heading towards the kitchen. “You want something to drink?” He asked.

“No, I’m good.” Jay said, leaning against his counter. 

“How are you feeling?” Will asked, taking a sip of the water bottle he got himself. 

Jay shrugged, “I’m good.” Will eyed him, “Listen man, I know we talked about it before, but I just want to make sure that it’s okay...again.” Jay thought back to what felt like a lifetime ago, a few days before Erin left for New York. 

_ Jay stood in front of the whiteboard with Will, looking through photos of victims from their recent drug case. “At least you guys get overtime.” Will said, before fishing in his pocket, Will pulled a red velvet box, surprising Jay. Will had seemed so against him proposing to Erin that he was sure he wouldn’t let him near their mom’s ring. “Mom’s ring. She always said it’s not a race, but whoever meets the right girl first gets the ring.” _

_ Jay took the box in his hands, chuckling. “Hmm.” His mom was so important to him, and having Erin wear her ring felt like the blessing they needed, like his mom was a part of it. _

_ Will watched his brother with caution, but smiled kindly. “You sure about this?” Jay stared blankly at him and Will nodded, he always knew he was the king of stupid questions. “You tell dad?” _

_ “Why do I have to tell dad? It’s mom’s ring, not his.” Jay rushed out, immediately jumping down his brother's throat. Kevin interrupted them before Will could say anything, but Jay walked away feeling confident in his decision.  _

And he was, maybe even as confident as he was now. Jay pulled the same velvet box out of his pocket and set it on the counter. “Will, I’m sure.” He said, and this time he had the words to express how he was feeling. “I’ve never been more sure of anything in my entire life, but I already had one chance with this ring and if you want it-”

“Jay.” Will said, cutting him off. “I know mom always said it wasn’t a race, but you won. Hailey is…”

“The most amazing person that I have ever met.” Jay sighed out.

Will laughed, “I was going to say ‘going to love it,’ but that works too.” 

Jay beamed at his brother, taking the box back in his hand. “She’s the one Will, I know it. And I never thought I would say this, but I wish I could tell dad.” 

Will placed a comforting hand on his brother’s back, “He knows man. They both do.” 

Jay took a big breath and laughed nervously. “I’m proposing.” He said.

“Yeah, you are.” Will said, sharing his brother’s obvious joy. All he ever wanted was for Jay to be happy, and he knew without a doubt that Hailey was it for him. 

“You think she’ll say yes?” Jay asked in a teasing voice. 

Will laughed loudly, “I’d say it’s a solid 80 percent.”

**...**

  
  


About an hour later Jay was back in his truck headed to Molly’s. It was almost seven o’clock, two hours from Hailey’s arrival and the unit had a lot to do before she got there. Almost like she could hear him thinking about her, he got a text.

**_Hailes: I know I’m bringing Trudy, but who is in charge of Mouch? Shouldn’t they be coming together?_ **

_ Shit.  _ He hadn’t thought of that. 

**_Jay: Ritter is getting Mouch. Don’t worry about it, we have a plan._ **

**_Hailes: Okay, whatever you say._ **

Jay sighed, he would admit a fake anniversary party was a little lame, but the only other thing he could think of was a fake baby shower and something told him that it wouldn’t really be appropriate to throw one of those in a bar.

**_Hailes: Also, “in charge” Jay is kinda sexy...you should help throw parties more often._ **

Jay smirked at his phone while he sat in the parking lot, shaking his head he texted back.

**_Jay: Good to know ;)_ **

**_Jay: Get ready for the best birthday of your life._ **

When he pulled the door open, he was met with Kim shouting orders at Herrmann, Mouch, Kevin and Adam. Most of the decorations were already hung and he was informed that there were ten bottles of champagne hidden behind the counter. 

“Wow. It looks amazing in here.” He looked at Kim directly. “Thank you.”

Kim grinned, “Of course! It’s not everyday that one of my oldest friends proposes to my best friend.” She says, playfully punching his arm. Vanessa had been gone for over a year and in that time Hailey and Kim had gotten really close, they all had. After years of losing one person after another, the members of intelligence felt more like a family than they ever had before. 

“This is crazy, isn’t it?” Jay asked, Adam and Kevin trickling into the conversation. 

“It’s a long time coming, that’s for sure.” Adam said, wrapping his arm around Kim. 

Kevin scoffed, “Oh, like you can talk.” He teased. 

Jay’s nerves got worse and worse, “This isn’t too much right?” Jay asked his friends, “You think she’ll like it?”

“Jay.” Kim said, gaining his attention. “You could slip a ring pop on Hailey’s finger in front of the district and she would love it, because she loves you. But this,” She gestures around the room, “this is beautiful and incredibly sweet  _ and  _ romantic. This is everything she deserves.” 

Jay smiles with pride, he wants to be everything she deserves, but Hailey Upton deserves the entire world and he wouldn’t mind spending his entire life trying to give her that. “Burgess, we just need to get you a t-shirt that says ‘I’m basically a hallmark card.’” Kevin says, motioning across his chest. 

“Let’s have a toast.” Kim says and on que Herrmann has glasses ready for them. 

Kevin raises his glass, “To the OGs.”

Kim rolls her eyes, but raises her glass as well, “To Jay and Hailey.” 

Jay raises his glass and so does Adam, giving a toast of his own. “To upstead.” 

Jay lowers his arm and glares at Adam, “Man, you have got to stop calling us that.”

“Anyway,” Kim says, “To love.”

“True love.” Adam interjects.

“Adam.” Kim snaps.

“What, you're the only one that gets to be a hallmark card? That’s not fair.”

“How about this,” Jay says, raising his glass again. “To me not shitting my pants before she gets here.”

They all laugh, “I’ll drink to that,” Kevin says shrugging and then all down their drinks. 

**…**

At eight forty-five Jay stood at the bar, his hands sweaty and his knees a little shaky. It was fifteen minutes until go time and he got more anxious by the second. He was pretty sure she was going to say yes, but he wanted it to be perfect for her. As perfect as she was for him. 

Most of their friends have arrived and were talking amongst themselves around the perimeter of the bar, leaving room for Hailey to eventually make her way down the middle to Jay. Everyone was buzzing, taking in the decorations and consuming copious amounts of alcohol, something that Jay had decided against doing even though he would love a beer (or five) right about now.

At three til nine, he got a text from Hailey stating that they had arrived and Jay shushed everyone, standing in the middle of the room to wait for his (hopefully) future wife. 

Hailey walked down the sidewalk with the desk sergeant, hiding her smile. She was excited to see what her friends had come up with for the happy couple. They reached the door and Hailey smirked at Trudy, “Hey sarge.”

“Upton?”

“Happy anniversary.”

This time Trudy smirked, “It isn’t my anniversary.”

“What-” Hailey started, but froze in her spot as she opened the door. The sight in front of her was breathtaking. The usual fairy lights were still hung up, but also hanging from the ceiling were hundreds of pictures, pictures of her and Jay. Hailey felt her eyes welling up with tears, she took a few steps forward, looking around to see all of her closest friends, her family. At a closer look, she could see all of the tables had empty bottles of various alcohols, all labeled with dates and cards with memories. 

He was grinning ear to ear, but when she saw him, it somehow got even bigger. “Jay.” She laughed out.

“Hey.” He said, meeting her in the middle of the room. 

“I hate to break it to you, but you decorated for the wrong couple.” She joked. 

“Oh no, really?” He gasped and Hailey laughed. 

Jay took her in, she was wearing her signature black jeans and a blue sweater. She looked as beautiful as ever, and he was ready. “Quite the crowd…” She whispered. 

“I know, I’m a little nervous.” He said, reaching out to take her hand in his. “Hailey Anne Upton, there are not enough words to describe how much I love you. And I have never been good at expressing my feelings, you know that better than anyone. But I have said it a million times and I will say it a million more: I would follow you anywhere. I looked at you and knew you were the most beautiful woman I have ever met. I looked at you and I trusted you, I have trusted  _ you _ since the day I met you. I look at you, and I’ve got it. I look at you and I see the rest of my life, I see that you are everything I have ever wanted and more. I look at you and I know that you are it for me, there will never be anyone like you Hailey.”

Hailey felt the tears begin to roll down her face, he used her own words against her. Jay reached in his pocket, pulling out just a ring. “This is my mother’s ring, and for so long she was the most important woman in my life. But she has been gone for a long time and Hailey you have taken that place, and she would have loved you. So,” Jay said, finally getting down on one knee. “Will you make me the luckiest man alive, and marry me?”

Hailey took a deep breath, trying to pull herself together. “Yes.” She choked out before launching herself into his arms. Jay caught her with ease and kissed her passionately as their friends cheered for them. Jay reluctantly set Hailey back down on the floor, pressing another kiss to her lips before stepping back and finally slipping the ring on her finger. 

“Perfect fit.” He said, pulling her to him and pressing a kiss to her forehead. “I love you.” He said, peeking down at her.

“I love you so much.” She hugged him tighter, “And I cannot wait to be your wife.”

“Let’s just elope, we can get married tomorrow.” Jay said.

Hailey scoffed, “That’s a funny joke, Kim would kill me.” 

“Good point.” He said, holding her tightly. “I’m thinking of a June wedding.”

“Did you really just say that?” Hailey burst out laughing.

Jay grimaced, “We don’t have to talk about it…”

Hailey turned to face him, pressing her palms to his chest. “How about this? We can get married whenever and wherever you want, as long as you wear your thigh holster during the whole ceremony.”

Jay gave her a shocked look, “Please tell me you aren’t kidding.”

Hailey got up on her tiptoes and whispered in his ear, “I’m dead serious.” 

“Thank God.”

The happy couple accepted some congratulations before sneaking over to the bar. It had turned into a full on party, Herrmann turned the music up and everything. “You know, Hailey Halstead has a nice ring to it.” She confessed as she leaned into Jay. 

“I think so.” He said, beaming at her.

“Excuse me everyone.” Kim said, clinking her glass as they were passed around to everyone. She raised hers, “To the happy couple, I love you both and I am so happy for you. We all are.”

“And to the fact that Jay didn’t shit his pants!” Adam interjected from beside her.

“What?” Hailey whispered under her breath.

“Don’t worry about it…” Jay muttered, mentally punching Adam in the face.

Kim shrugged, “Sure.” They all raised their glasses and cheered. Jay set his and Hailey’s down and dipped her dramatically, bringing his lips to hers once again.

“I love you Jay Halstead,” She said as he brought her back to a standing position.

“I love you too, the future Mrs. Hailey Halstead.”

  
  


**Author's Note:**

> I watched the clip from 4x23 and then debated posting this idea just as a discussion comment, but then I was like “why not” and I just wrote it! I’m so glad I did, I wrote it so fast and loved writing it. I also hope that this didn’t come off as Erin bashing, I try not to write like that. I was the biggest linstead fan and I still love Erin, I just have moved on from linstead and wanted to show the potential parallels. Anyway, I promise I will update Lost or Found soon, it’s been crazy the past few months and I honestly haven’t had the motivation to write, but the scooby gang will be back soon! Thank you so much for reading! <3


End file.
